Asymmetric Baylis Hillman Reaction Research Articles

ChemInform Abstract: An Enantio‐ and Stereocontrolled Synthesis of (‐)‐Mycestericin E via Cinchona Alkaloid Catalyzed Asymmetric Baylis—Hillman Reaction.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The use of enantiomerically pure N-sulfinimines in asymmetric Baylis–Hillman reactions

The electrophilic behaviour of enantiomerically pure N- p-toluenesulfinimines ( 1a– d ) and N- tert-butanesulfinimine 2 has been tested in the asymmetric Baylis–Hillman reaction with methyl acrylate with and without Lewis acids. In the presence of In(OTf) 3 good yields and high diastereoselectivities have been achieved providing an effective route to β-amino-α-methylene esters.

ChemInform Abstract: Asymmetric Baylis—Hillman Reaction Using Sugar Acrylates — Synthesis of Optically Active α‐Methylene‐β‐hydroxy Alkanoates.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Asymmetric Baylis–Hillman reaction using sugar acrylates—synthesis of optically active α-methylene-β-hydroxy alkanoates

A study on the asymmetric Baylis–Hillman reaction of three chiral acrylates; 1,2:5,6-di- O- iso-propylidine-α- d-glucofuranose-3-acrylate 1, 2,3:5,6-di- O- iso-propylidine-α- d-mannofuranose-1-acrylate 2 and 1,2- O- iso-propylidine-5- O- tert-butyldimethylsilyl-α- d-xylofuranose-3-acrylate 3, with various aldehydes was conducted, resulting in adducts with moderate diastereoselectivity (5–40% e.e.).

An enantio- and stereocontrolled synthesis of (-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction.

A new enantiocontrolled synthesis of a potent immunosuppressant(-)-mycestericin E has been accomplished by using cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction of an aldehyde with 1,1,1,3,3,3-hexafluoroisopropyl acrylate and Lewis acid-promoted cyclisation of an epoxytrichloroacetimidate as the key steps.

ChemInform Abstract: Chiral Amine‐Catalyzed Asymmetric Baylis—Hillman Reaction: A Reliable Route to Highly Enantiomerically Enriched (α‐Methylene‐β‐hydroxy)esters.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Asymmetric Baylis—Hillman Reactions of Novel Bornyl Acrylate Esters.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Asymmetric Baylis-Hillman Reactions of Novel Bornyl Acrylate Esters

3, 3-(2, 3-Butanedioxy)-2-exo-bornyl acrylate esters have been prepared from D-(+)-camphor and reacted with a range of aldehydes to afford the corresponding Baylis-Hillman products in up to 34% d.e.

Enantiospecific generation of anti-aldol adducts via conjugate addition to 5-methylene-1,3-dioxan-4-ones

Abstract Michael additions to the exocyclic olefins of optically pure dioxanones (prepared via the asymmetric Baylis-Hillman reaction) are studied. The products can be obtained in excellent diastereoselectivity to ultimately provide products equivalent to those derived via anti aldol additions. Quaternary centers can also be created with good selectivity via this protocol.

ChemInform Abstract: The Asymmetric Baylis—Hillman Reaction as a Template in Organic Synthesis.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Asymmetric Baylis–Hillman reactions: catalysis using a chiral pyrrolizidine base

A novel chiral pyrrolizidine base 5 derived from L-proline promotes the Baylis–Hillman reaction of ethyl and methyl vinyl ketones with electron deficient aromatic aldehydes with moderate levels of enantiomeric excess.

The asymmetric Baylis-Hillman reaction as a template in organic synthesis

The Baylis-Hillman reaction of camphor-based acrylates has been demonstrated to result in the formation of products with high optical purity. A model that explains these results and the use of these products in the formation of anti aldol adducts is discussed.

Effective enantioselective approach to α-aminoalkylacrylic acid derivatives via a synthetic equivalent of an asymmetric Baylis–Hillman reaction: application to the synthesis of two C-2′ hydroxymethyl analogues of docetaxel

Download options Please wait... Article information DOI https://doi.org/10.1039/P19960002869 Article type Paper Download Citation J. Chem. Soc., Perkin Trans. 1, 1996, 2869-2872 BibTex EndNote MEDLINE ProCite ReferenceManager RefWorks RIS Permissions Request permissions Effective enantioselective approach to α-aminoalkylacrylic acid derivatives via a synthetic equivalent of an asymmetric Baylis–Hillman reaction: application to the synthesis of two C-2′ hydroxymethyl analogues of docetaxel Y. Génisson, C. Massardier, I. Gautier-Luneau and A. E. Greene, J. Chem. Soc., Perkin Trans. 1, 1996, 2869 DOI: 10.1039/P19960002869 To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page. If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given. If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page. Read more about how to correctly acknowledge RSC content. Search articles by author Yves Génisson Christine Massardier Isabelle Gautier-Luneau Andrew E. Greene

Asymmetric Baylis-Hillman reactions using chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes catalysts under high pressure conditions

Chiral C 2-symmetric 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes (DABCOs) ( 1) have been utilized as catalysts for asymmetric Baylis-Hillman reactions. Optically active α-methylene-β-hydroxyalkanone was obtained in up to 47% ee. Under high pressure conditions, a remarkable enhancement of both reaction rate and enantioselectivity has been observed.